Sphingoglycolipid compounds and therapeutic uses thereof

Abstract

The present invention relates to a sphingoglycolipid represented by the formula (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.5 represent H or a specific monosaccharide; R.sub.3 and R.sub.6 represent H or OH, respectively;R.sub.4 represents H, OH or a specific monosaccharide;X denotes an integer from 19 to 23;R.sub.7 represents any one of the following groups (a)-(g):(a) --(CH.sub.2).sub.11 --CH.sub.3,(b) --(CH.sub.2).sub.12 --CH.sub.3,(c) --(CH.sub.2).sub.13 --CH.sub.3,(d) --(CH.sub.2).sub.9 --CH(CH.sub.3).sub.2,(e) --(CH.sub.2).sub.10 --CH(CH.sub.3).sub.2,(f) --(CH.sub.2).sub.11 --CH(CH.sub.3).sub.2,(g) --(CH.sub.2).sub.11 --CH(CH.sub.3)--C.sub.2 H.sub.5.

Claims

1. A sphingoglycolipid represented by the formula (I): ##STR9## wherein R.sub.1, represents H or ##STR10## R.sub.2 represents H, ##STR11## R.sub.3 and R.sub.6 represent H or OH, respectively; R.sub.4 represents H,, OH, or ##STR12## R.sub.5 represents H or ##STR13## X denotes an integer from 19 to 23; and R.sub.7 represents any one of the following groups (a)-(g):

(a) --(CH.sub.2).sub.11 --CH.sub.3,

(b) --(CH.sub.2).sub.12 --CH.sub.3,

(c) --(CH.sub.2).sub.13 --CH.sub.3,

(d) --(CH.sub.2).sub.9 --CH(CH.sub.3).sub.2,

(e) --(CH.sub.2).sub.10 --CH(CH.sub.3).sub.2,

(f) --(CH.sub.2).sub.11 --CH(CH.sub.3).sub.2,

(g) --(CH.sub.2).sub.11 --CH(CH.sub.3)-C.sub.2 H.sub.5,

wherein at least one of R.sub.1, R.sub.2, R.sub.4 and R.sub.5 is a glycosyl moiety.

2. A sphingoglycolipid represented by the formula (II): ##STR14## wherein R.sub.8 represents H or OH and if R.sub.8 represents OH, R.sub.9 represents H, and if R.sub.8 represents H, R.sub.9 represents OH;

R.sub.10 represents H or OH and if R.sub.10 represents OH, R.sub.11 represents H, and if R.sub.10 represents H, R.sub.11 represents OH;

R.sub.12 represents H or OH;

X denotes an integer from 19 to 23; and

Y denotes an integer from 11 to 13.

3. A sphingoglycolipid represented by the formula (III): ##STR15## wherein R.sub.13 represents OH or H and if R.sub.13 represents OH, R.sub.14

represents H, and if R.sub.13 represents H, R.sub.14 represents OH;

R.sub.15 represents H or OH;

X denotes an integer from 19 to 23; and

Y denotes an integer from 11 to 13.

5. A sphingoglycolipid according to claim 4, which is selected from the group consisting of the following compounds:

O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-O-.alpha.-D-glucopyranosyl-(1.fwd arw.1)-(2S,3S,4R)-2-amino-N-hexacosanoyl-1,3,4-octadecanetriol;

O-.alpha.-D-galactopyranosyl-(1.fwdarw.6)-O-.alpha.-D-galactopyranosyl-(1.f wdarw.1)-(2S,3S,4R)-2-amino-N-hexacosanoyl-1,3,4-octadecanetriol; and

O-.alpha.-D-glucopyranosyl-(1.fwdarw.4)-O-.alpha.-D-glucopyranosyl-(1.fwdar w.1)-(2S,3S,4R)-2-amino-N-hexacosanoyl-1,3,4-octadecanetriol.

6. A pharmaceutical composition comprising the sphingoglycolipid described in claim 1 as an effective ingredient and a pharmaceutically acceptable carrier or diluent.

7. A pharmaceutical composition comprising the sphingoglycolipid described in claim 2 as an effective ingredient and a pharmaceutically acceptable carrier or diluent.

8. A pharmaceutical composition comprising the sphingoglycolipid described in claim 3 as an effective ingredient and a pharmaceutically acceptable carrier or diluent.

9. A pharmaceutical composition comprising the sphingoglycolipid described in claim 4 as an effective ingredient and a pharmaceutically acceptable carrier or diluent.

10. A pharmaceutical composition comprising the sphingoglycolipid described in claim 5 as an effective ingredient and a pharmaceutically acceptable carrier or diluent.

11. A process for inhibiting tumor growth wherein an effective amount of the sphingoglycolipid described in claim 1 is administered to a patient who needs inhibition of tumor growth.

12. A process for promoting proliferation of bone marrow cells, wherein an effective amount of the sphingoglycolipid described in claim 1 is administered to a patient who needs promotion of the proliferation of bone marrow cells.

13. A process for stimulation of the immune system, wherein an effective amount of the sphingoglycolipid described in claim 1 is administered to a patient who needs stimulation of the immune system.